Wool azo dye.



' of philosophy,

UNITED STATES PATENT OFFICE.

LEOPQLD 311852, 0! VO HWINKEL NEAR'ELBEBFELD BENIABBIKEN VOEK. FBIEDB. BAYER & 00., O1

rona'rrox OF GEM.

GERMANY, ABSIGNOR TO FAR- iannnnrsnncsnmmr, A COE- WOOL AZO DYE.

1,054,348. 80 Drawing.

Specification of mm; nun. Application fledjnly 2, 1912. Bertal'lmJWJlSO.

Patented Feb. 25.1 913.

To all whom'it may comma Be it known that Ll'lmorow Hnssa, doctor chemist, citizen of the German Em ire, residin atpvohwinkelfnear Elberfel ,Germany, ave invented new and useful Improvements in Wool Azo Dye, of which the following is a specification.

I have found that new and valuable monoazo dyestufis for wool fast to washing can be obtained by combining diazo compounds of the naphthalene series, such as diaaot-ized naphthylamins, aminona ht-hols or their sulfonic acids with al enzylmeta-toluidin-sulfonic acids. The yes have most probably the formula:

6H] (R=alky1; R'..-=a radical of the naphtha- I lene series, such as cum-.camsom-pus m.

5018 thus obtained are after being dried and mlverized in the shape of their alkaline sa ts from vellow to red powder soluble in water. They yield upon reduction with stunnous chlorid and h 'clrochloric acid a nuphth 'lami'n compoun and 3'methyl-4-amino-1-al yl-benzyl anilin-sulfonic acid:

- They dye wool from acid baths from yellow to violet shades fast to washing. A

The following example may illustrate my invention; the parts being by weightz-QQB parts of Lb-naphthylamin sulfonic acid are diazotized with 69 parts of sodium nitrite and 280 rts of hydrochloric acid (30 per centl) he diazo compound. thus obtained is then added to-,a solution of 327'parts of thylbenzyl-meta-toluidin-sulfonic acid (sodium salt) and 180 parts of calcined soda in 8000 parts of water.- The dye is salted out with common salt, filtered off and dried.

The new dyes The new dye having most probably the formula: c an N-N- -u-ca;-c.u.-so.n

dome is after being dried and pulverized in the sha e of its sodium salt an orange powder easily soluble in water with an orange coloration, soluble -in concentrated sulfuric acid with a red coloration. It yields u on reduction with stannous chlorid and by rochloric acid l-napthylamin-5-sulfonic acid and 3-mothyl-4-amino-l-ethylbenzylanilinsulfonic acid. It dyes wool an orange-red.

Other diazo compounds may be used e. g. the 'diazo compounds of 4'-toluidin-2-sulfon l-l-naphthylamin- 5 -sulfonic acid, 1- nap thlylam'in-2- or 4-sulfonic acid, Q-naphthylamin 4.8-disu'lfonic acid, 1.8 aminonaphthol-3.G-disulfonic acid, acety1-L4-na hth lendiamin-G-sulfonic acid etc. or ot er al yl benzyl meta-toluidin-sulfonic acids 0. r the methyl-benzyl-meta-toluidin-sulfonic acid.

For the purpose it is to be assumed. that any product which a diazotized nap thylamin compound and an alk l-benzyl-to uldin-sulfonic acid .con-

may be obtained from tains te generic formula:

such bein in accordance with my resent understant ing as a chemist andsuc being the generic scope of the patent.

I-claim:-

1. The herein described new monoazo d stufl's having probably the general formui a:

R'=a radical of the naphthalene series,

=an alkyl) which dyes are after being 100 Corrections in Letters Patent No. 1,054,348.

dried and u1verized in the shape of their alkaline sa s from yellow to red powders soluble in water: yieldinqlu n reduction with stannous chlorid and y rochloric acid a naphthylamin compound and B-methyl-ion! v which'dye is after being dried and pulveracid and 3-methyl-4-amino-l-ethyl-benzylanilin-sulfonic acid and d eing wool from acid baths orange to re shades fast to washing, substantally as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

LEOPOLD HESSE. 1,. 8.

Witnesses Hanan Norma, Amna'r NUm.

. Copies of this patent may be obtained for are cents each, by addressing the Oommiutoner of intents,

Washington, D. 0."

case in the Patent Oflice.

[sans] It is hereby certified that in Letters Patent No. 1,054,848, granted February 25, 191?, upon the application of Leopold Hesse, of Vohwinkel, near Elberfeld, Germany, for an improvement in Wool Azo Dyef errors appear in the printed speci fioation requiring correction as follows: Page 1, line 13, for the word alky read alky l; same page, line 23, in formula, for the symbols C,,I'1,SO,H read ONES QB; earns page, lines 28-29, for the word powder read powders, and line47, for the word ,thylhenzy l read etbylbenzyly' and that the said Letters Patent ahohld be read with these corrections therein that 'the some may conform to the record of the Signed and sealed this 6th day of May, A. D., 1918.

G. C. BILLINGS,

Acting Obmmiuioner of Patents.

Corrections in Letters Patent No. 1,054,348.

dried and u1verized in the shape of their alkaline sa s from yellow to red powders soluble in water: yieldinqlu n reduction with stannous chlorid and y rochloric acid 5 a naphthylamin compound and B-methyl-ion! v which'dye is after being dried and pulveracid and 3-methyl-4-amino-l-ethyl-benzylanilin-sulfonic acid and d eing wool from acid baths orange to re shades fast to washing, substantally as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

LEOPOLD HESSE. 1,. 8.

Witnesses Hanan Norma, Amna'r NUm.

. Copies of this patent may be obtained for are cents each, by addressing the Oommiutoner of intents,

Washington, D. 0."

case in the Patent Oflice.

[sans] It is hereby certified that in Letters Patent No. 1,054,848, granted February 25, 191?, upon the application of Leopold Hesse, of Vohwinkel, near Elberfeld, Germany, for an improvement in Wool Azo Dyef errors appear in the printed speci fioation requiring correction as follows: Page 1, line 13, for the word alky read alky l; same page, line 23, in formula. for the symbols C,,I'1,SO,H read O' HZS 0,H; earns page, lines 28-29, for the word powder read powders, and line47, for the word ,thylhenzy l read etbylbenzyly' and that the said Letters Patent ahohld be A read with these corrections therein that 'the some may conform to the record of the Signed and sealed this 6th day of May, A. D., 1918.

G. C. BILLINGS,

Acting Obmmiuioner of Patents. 

